EP2527318A1 - Monoaminofluorene compound and organic light-emitting device using the same - Google Patents

Monoaminofluorene compound and organic light-emitting device using the same Download PDF

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EP2527318A1
EP2527318A1 EP12171470A EP12171470A EP2527318A1 EP 2527318 A1 EP2527318 A1 EP 2527318A1 EP 12171470 A EP12171470 A EP 12171470A EP 12171470 A EP12171470 A EP 12171470A EP 2527318 A1 EP2527318 A1 EP 2527318A1
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group
substituted
ph
groups
direct bond
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French (fr)
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EP2527318B1 (en
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Akihito Saito
Mizuho Hiraoka
Koichi Suzuki
Akihiro Senoo
Hiroshi Tanabe
Naoki Yamada
Chika Negishi
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Canon Inc
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Canon Inc
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Abstract

Novel monoaminofluorene compounds are provided, and organic light-emitting devices which exhibit good luminescence hue of extremely high purity and have optical output with high luminescence efficiency, high luminance and longer operating life are provided using the compounds. The monoaminofluorene compound represented by the following general formula [1]:

Description

    Technical Field
  • The present invention relates to a monoaminofluorene compound and an organic light-emitting device, more particularly to a light-emitting device using an organic compound which emits light by applying an electric field to a thin film of the organic compound.
  • Background Art
  • An organic light-emitting device is a device having a thin film containing a fluorescent organic compound interposed between an anode and a cathode, in which excitons of the fluorescent compound are generated by injecting electrons and holes (positive holes) from each electrode into the compound and the light emitted when these excitons return to the ground state is utilized.
  • In a research by Eastman Kodak Company in 1987 (Appl. Phys. Lett. 51, 913 (1987)), luminescence on the order of 1000 cd/m2 upon application of voltage on the order of 10 V was reported in relation to a device having a function separate type two-layer structure using ITO for the anode, and magnesium silver alloy for the cathode, respectively, and using aluminum quinolinol complex as an electron-transporting material as well as a light-emitting material and triphenylamine derivative as a hole-transporting material. Relevant patents include U.S. Patent No. 4,539,507 , U.S. Patent No. 4,720,432 , U.S. Patent No. 4,885,211 , etc.
  • Moreover, luminescence ranging from ultraviolet to infrared rays can be obtained by changing the kind of fluorescent organic compound, and, recently, studies on various compounds are actively conducted. For example, such studies are described in U.S. Patent No. 5,151,629 , U.S. Patent No. 5,409,783 , U.S. Patent No. 5,382,477 , Japanese Patent Application Laid-Open No. 2-247278 , Japanese Patent Application Laid-Open No. 3-255190 , Japanese Patent Application Laid-Open No. 5-202356 , Japanese Patent Application Laid-Open No. 9-202878 , Japanese Patent Application Laid-Open No. 9-227576 , etc.
  • In addition to the organic light-emitting devices using low molecular materials as mentioned above, an organic light-emitting device using a conjugated polymer was reported by a group in Cambridge University (Nature, 347, 539 (1990)). This report confirms that luminescence occurs in a single layer film which is formed of poly (phenylene vinylene) (PPV) using a coating system. Related patents of the organic light-emitting device using conjugated polymer include U.S. Patent No. 5,247,190 , U.S. Patent No. 5,514,878 , U.S. Patent No. 5,672,678 , Japanese Patent Application Laid-Open No. 4-145192 , Japanese Patent Application Laid-Open No. 5-247460 , etc.
  • The latest progress in the organic light-emitting device is remarkable in this way, and the features thereof facilitate production of light-emitting devices imparted with high luminance at low applied voltage, diversity of luminescence wavelength, high-speed response, thin shape and lightweight, thereby suggesting possibility for a wide variety of applications.
  • However, there still remain many problems in respect of durability, such as change with the passage of time by prolonged use, degradation by atmospheric gas containing oxygen, humidity, etc. Furthermore, when the application to a full color display and the like is envisaged, optical output of further higher luminance or higher conversion efficiency, and luminescence in blue, green and red of high color purity are required under the present condition.
  • For example, although diamine compounds as a luminescent material were disclosed in Japanese Patent Application Laid-Open No. 2001-52868 , blue luminescence of high color purity (chromaticity coordinate: x, y = 0.14-0.15, 0.09-0.10) was not obtained. An example using a compound having the similar diamino structure was also disclosed in Japanese Patent Application Laid-Open No. 2001-196177 , but the compound was used as a hole injection layer, and there was no description of the use as a light-emitting layer and light-emitting properties thereof such as luminescence color and efficiency.
  • DISCLOSURE OF THE INVENTION
  • The present invention has been made to solve these problems of the prior art, and an object of the present invention is to provide a novel monoamino compound.
  • Another object of the present invention is to provide an organic light-emitting device exhibiting good luminescence hue of extremely high purity and high luminance optical output with a high efficiency and a longer operating life.
  • Still another object of the present invention is to provide an organic light-emitting device which can be readily manufactured at relatively low cost.
  • The inventors of the present invention conducted intensive study in order to solve the above-mentioned problems and came to complete the present invention.
  • That is, the monoaminofluorene compound of the present invention is characterized in that it is represented by the following general formula [1] or [2].
    Figure imgb0001
    wherein X1 is a divalent group selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, and alkylene, aralkylene, alkenylene, amino, silyl, carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, or X1 may be a direct bond;
    X2 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group and a cyano group;
    Y1 and Y2 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y1 and Y2, or X1, Y1 and Y2 may also join together to form a ring;
    R1 and R2 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    n is an integer of 2 to 10 when X1 is a direct bond and X2 is a hydrogen atom, and otherwise an integer of 1 to 10.
    Figure imgb0002
    wherein X3 and X4 may be the same or different and are divalent groups selected from the group consisting of a substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, unsubstituted carbonyl, ether and thioether groups, or X3 may be a direct bond;
    X5 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group, and a cyano group;
    Y3 and Y4 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y3 and Y4, or X3, Y3 and Y4 may also join together to form a ring;
    R3 to R6 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    each of p and q is an integer not less than one and p+q is an integer of 2 to 10.
  • In the organic light-emitting device of the present invention comprising a pair of electrodes which consist of an anode and a cathode and one or more layers which are interposed between the electrodes and contain an organic compound, the at least one layer containing the organic compound preferably contains at least one compound represented by the above-mentioned general formula [1] or [2].
  • BRIEF DESCRIPTION OF DRAWINGS
    • Fig. 1 is a cross-sectional view showing an example of the organic light-emitting device according to the present invention;
    • Fig. 2 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention;
    • Fig. 3 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention;
    • Fig. 4 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention;
    • Fig. 5 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention; and
    • Fig. 6 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention.
    BEST MODE FOR CARRYING OUT THE INVENTION
  • The present invention will be described in detail below.
  • The monoaminofluorene compound of the present invention is described first.
  • The monoaminofluorene compound of the present invention is represented by the above-mentioned general formula [1] or [2].
  • The monoaminofluorene compound of the present invention can mainly be used as an organic light-emitting device material, and when it is used as a light-emitting device material, devices having high color purity, high luminescence efficiency and a longer operating life can respectively be obtained even in a single layer. Furthermore, a luminescence spectrum with a narrower half-value width, i.e., luminescence more excellent in color purity is obtained by introducing fluorene having a rigid structure into the main chain of the molecule. Furthermore, since the Stokes shift is suppressed, a shift of the luminescence wavelength is suppressed, and it is also possible to shift the absorption even toward a longer wavelength side, and when it is used as a dopant material, use of a host material which has a luminescence spectrum in a relatively longer wavelength side is also enabled.
  • Each of the monoaminofluorene compounds of the present invention can be used for the purpose of both dopant material and host material in a light-emitting layer to provide a device having high color purity, high luminescence efficiency, and longer operating life, and in particular can be used as a dopant material in combination with a suitable host material of easily causing energy transfer to provide a device holding high color purity luminescence and having higher efficiency.
  • Specific examples of the substituents in the above-mentioned general formulae [1] and [2] are shown below.
  • Examples of the substituted or unsubstituted linear or cyclic alkyl group include methyl group, ethyl group, n-propyl group, n-butyl group, n-hexyl group, n-decyl group, iso-propyl group, iso-butyl group, tert-butyl group, tert-octyl group, trifluoromethyl group, cyclohexyl group, cyclohexylmethyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted aralkyl group include benzyl group, phenethyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted aryl group include phenyl group, 4-methylphenyl group, 4-methoxyphenyl group, 4-ethylphenyl group, 4-fluorophenyl group, 3,5-dimethylphenyl group, triphenylamino group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, tetracenyl group, pentacenyl group, fluorenyl group, triphenylenyl group, perylenyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted heterocyclic ring group include pyrrolyl group, pyridyl group, bipyridyl group, methylpyridyl group, terpyrrolyl group, thienyl group, terthienyl group, propyl thienyl group, furyl group, quinolyl group, carbazolyl group, oxazolyl group, oxadiazolyl group, thiazolyl group, thiadiazolyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted alkylene group include methylene group, ethylene group, propylene group, iso-propylene group, butylene group, tert-butylene group, hexylene group, heptylene group, cyclohexylene group, cyclohexylmethylene group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted aralkylene group include benzylene group, phenylethylene group, phenethylene group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted arylene group include phenylene group, biphenylene group, 2,3,5,6-tetrafluorophenylene group, 2,5-dimethylphenylene group, naphtylene group, anthracenylene group, phenanthrenylene group, tetracenylene group, pentacenylene group, perylenylene group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted divalent heterocyclic ring group include furanylene group, pyrrolylene group, pyridinylene group, terpyridinylene group, thiophenylene group, terthiophenylene group, oxazolylene group, thiazolylene group, carbazolylene, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted alkenyl group include vinyl group, allyl group (2-propenyl group), 1-propenyl group, iso-propenyl group, 2-butenyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted amino group include amino group, methylamino group, ethylamino group, dimethylamino group, diethylamino group, methylethylamino group, benzylamino group, methylbenzylamino group, dibenzylamino group, anilino group, diphenylamino group, phenyltolylamino group, ditolylamino group, dianisolylamino group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted carbonyl group include acetyl group, propionyl group, isobutyryl group, methacryloyl group, benzoyl group, naphtoyl group, anthranyl group, toluoyl group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted alkoxy group include methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-butylphenoxy group, benzyloxy group, but, of course, are not limited to these.
  • Examples of the substituted or unsubstituted sulfide group include methylsulfide group, ethylsulfide group, phenylsulfide group, 4-methylphenylsulfide group, but, of course, are not limited to these.
  • Examples of the substituent group which the above-mentioned substituent groups may have include alkyl groups such as methyl group, ethyl group, n-propyl group, iso-propyl group, ter-butyl group, octyl group, benzyl group and phenethyl group, an aralkyl group, alkoxy groups such as methoxy group, ethoxy group, propoxy group, 2-ethyl-octyloxy group, phenoxy group, 4-butylphenoxy group and benzyloxy group, aryl groups such as phenyl group, 4-methylphenyl group, 4-ethylphenyl group, 3-chlorophenyl group, 3,5-dimethylphenyl group, triphenylamino group, biphenyl group, terphenyl group, naphthyl group, anthryl group, phenanthryl group and pyrenyl group, a heterocyclic ring group such as pyridyl group, bipyridyl group, methylpyridyl group, thienyl group, terthienyl group, propylthienyl group, furyl group, quinolyl group, carbazolyl group and N-ethylcarbazolyl group, a halogen group, cyano group, and nitro group, but, of course, are not limited to these.
  • Typical examples of the compound represented by the general formulae [1] and [2] are shown below but are not limited to these compounds.
    Figure imgb0003
    [Table 1]
    n R1, R2 X1 X2 Y1 Y2
    1 1 Me Direct bond Ph Ph Ph
    2 1 Me Direct bond Ph
    Figure imgb0004
    Figure imgb0005
    3 1 Me Direct bond Ph Ph
    Figure imgb0006
    4 1 Me Direct bond Ph Ph
    Figure imgb0007
    5 1 Me Direct bond Ph Ph
    Figure imgb0008
    6 1 Me Direct bond Ph Ph
    Figure imgb0009
    7 1 Me Direct bond Ph Ph
    Figure imgb0010
    8 1 Me Direct bond Ph Ph
    Figure imgb0011
    9 1 Me Direct bond
    Figure imgb0012
    Figure imgb0013
    Figure imgb0014
    10 1 Me Direct bond
    Figure imgb0015
    Figure imgb0016
    Figure imgb0017
    11 1 Me Direct bond
    Figure imgb0018
    Figure imgb0019
    Figure imgb0020
    12 1 Me Direct bond
    Figure imgb0021
    Figure imgb0022
    Figure imgb0023
    13 1 Me
    Figure imgb0024
    H
    Figure imgb0025
    Figure imgb0026
    14 1 Me
    Figure imgb0027
    H
    Figure imgb0028
    Figure imgb0029
    15 1 Me
    Figure imgb0030
    H Ph
    Figure imgb0031
    16 1 Me
    Figure imgb0032
    H Ph
    Figure imgb0033
    17 1 Me
    Figure imgb0034
    H Ph
    Figure imgb0035
    18 1 Me
    Figure imgb0036
    H Ph
    Figure imgb0037
    19 1 Me
    Figure imgb0038
    Ph Ph Ph
    20 1 Me
    Figure imgb0039
    Ph
    Figure imgb0040
    Figure imgb0041
    [Table 2]
    n R1, R2 X1 X2 Y1 Y2
    21 1 Me
    Figure imgb0042
    Ph Ph
    Figure imgb0043
    22 1 Me
    Figure imgb0044
    Ph Ph
    Figure imgb0045
    23 1 Me
    Figure imgb0046
    Figure imgb0047
    Figure imgb0048
    Figure imgb0049
    24 1 Me
    Figure imgb0050
    Figure imgb0051
    Figure imgb0052
    Figure imgb0053
    25 1 Me
    Figure imgb0054
    Figure imgb0055
    Ph
    Figure imgb0056
    26 1 Me
    Figure imgb0057
    Figure imgb0058
    Figure imgb0059
    Figure imgb0060
    27 1 Me
    Figure imgb0061
    Figure imgb0062
    Figure imgb0063
    Figure imgb0064
    28 1 Me
    Figure imgb0065
    Figure imgb0066
    Ph
    Figure imgb0067
    29 1 Me
    Figure imgb0068
    H
    Figure imgb0069
    Figure imgb0070
    30 1 Me
    Figure imgb0071
    H
    Figure imgb0072
    Figure imgb0073
    31 1 Me
    Figure imgb0074
    Figure imgb0075
    Figure imgb0076
    Figure imgb0077
    32 1 Me
    Figure imgb0078
    H
    Figure imgb0079
    Figure imgb0080
    33 1 Me
    Figure imgb0081
    H
    Figure imgb0082
    Figure imgb0083
    34 1 Me
    Figure imgb0084
    H
    Figure imgb0085
    Figure imgb0086
    35 1 Me
    Figure imgb0087
    Figure imgb0088
    Figure imgb0089
    Figure imgb0090
    36 1 Me
    Figure imgb0091
    H
    Figure imgb0092
    Figure imgb0093
    [Table 3]
    n R1, R2 X1 X2 Y1 Y2
    37 1 Me
    Figure imgb0094
    H
    Figure imgb0095
    Figure imgb0096
    38 1 n-Bu
    Figure imgb0097
    H
    Figure imgb0098
    Figure imgb0099
    39 1 n—Bu
    Figure imgb0100
    Figure imgb0101
    Figure imgb0102
    Figure imgb0103
    40 1 Ph
    Figure imgb0104
    H
    Figure imgb0105
    Figure imgb0106
    41 1 Ph
    Figure imgb0107
    Figure imgb0108
    Figure imgb0109
    Figure imgb0110
    42 2 Me Direct bond H Ph Ph
    43 2 Me Direct bond H
    Figure imgb0111
    Figure imgb0112
    44 2 Me Direct bond H
    Figure imgb0113
    Figure imgb0114
    45 2 Me Direct bond H Ph
    Figure imgb0115
    46 2 Me Direct bond H Ph
    Figure imgb0116
    47 2 Me Direct bond H Ph
    Figure imgb0117
    48 2 Me Direct bond H Ph
    Figure imgb0118
    49 2 Me Direct bond H Ph
    Figure imgb0119
    50 2 Me Direct bond H Ph
    Figure imgb0120
    51 2 Me Direct bond Ph
    Figure imgb0121
    Figure imgb0122
    52 2 Me Direct bond Ph Ph
    Figure imgb0123
    53 2 Me Direct bond Ph Ph
    Figure imgb0124
    54 2 Me Direct bond Ph Ph
    Figure imgb0125
    55 2 Me Direct bond
    Figure imgb0126
    Figure imgb0127
    Figure imgb0128
    56 2 Me Direct bond
    Figure imgb0129
    Figure imgb0130
    Figure imgb0131
    [Table 4]
    n R1, R2 X1 X2 Y1 Y2
    57 2 Me Direct bond
    Figure imgb0132
    Figure imgb0133
    Figure imgb0134
    58 2 Me Direct bond
    Figure imgb0135
    Figure imgb0136
    Figure imgb0137
    59 2 Me
    Figure imgb0138
    H Ph Ph
    60 2 Me
    Figure imgb0139
    H
    Figure imgb0140
    Figure imgb0141
    61 2 Me
    Figure imgb0142
    H
    Figure imgb0143
    Figure imgb0144
    62 2 Me
    Figure imgb0145
    H Ph
    Figure imgb0146
    63 2 Me
    Figure imgb0147
    H Ph
    Figure imgb0148
    64 2 Me
    Figure imgb0149
    H Ph
    Figure imgb0150
    65 2 Me
    Figure imgb0151
    H Ph
    Figure imgb0152
    66 2 Me
    Figure imgb0153
    H Ph
    Figure imgb0154
    67 2 Me
    Figure imgb0155
    H Ph
    Figure imgb0156
    68 2 Me
    Figure imgb0157
    H Ph
    Figure imgb0158
    69 2 Me
    Figure imgb0159
    Ph Ph Ph
    70 2 Me
    Figure imgb0160
    Ph
    Figure imgb0161
    Figure imgb0162
    71 2 Me
    Figure imgb0163
    Ph Ph
    Figure imgb0164
    72 2 Me
    Figure imgb0165
    Ph Ph
    Figure imgb0166
    73 2 Me
    Figure imgb0167
    Ph Ph
    Figure imgb0168
    74 2 Me
    Figure imgb0169
    Figure imgb0170
    Figure imgb0171
    Figure imgb0172
    75 2 Me
    Figure imgb0173
    Figure imgb0174
    Figure imgb0175
    Figure imgb0176
    76 2 Me
    Figure imgb0177
    Figure imgb0178
    Ph
    Figure imgb0179
    [Table 5]
    n R1, R2 X1 X2 Y1 Y2
    77 2 Me
    Figure imgb0180
    Figure imgb0181
    Figure imgb0182
    Figure imgb0183
    78 2 Me
    Figure imgb0184
    Figure imgb0185
    Figure imgb0186
    Figure imgb0187
    79 2 Me
    Figure imgb0188
    Figure imgb0189
    Ph
    Figure imgb0190
    80 2 Me
    Figure imgb0191
    H
    Figure imgb0192
    Figure imgb0193
    81 2 Me
    Figure imgb0194
    H
    Figure imgb0195
    Figure imgb0196
    82 2 Me
    Figure imgb0197
    Figure imgb0198
    Figure imgb0199
    Figure imgb0200
    83 2 Me
    Figure imgb0201
    H
    Figure imgb0202
    Figure imgb0203
    84 2 Me
    Figure imgb0204
    H
    Figure imgb0205
    Figure imgb0206
    85 2 Me
    Figure imgb0207
    H
    Figure imgb0208
    Figure imgb0209
    86 2 Me
    Figure imgb0210
    Figure imgb0211
    Figure imgb0212
    Figure imgb0213
    87 2 Me
    Figure imgb0214
    H
    Figure imgb0215
    Figure imgb0216
    88 2 Me
    Figure imgb0217
    H
    Figure imgb0218
    Figure imgb0219
    89 2 n-Bu
    Figure imgb0220
    H
    Figure imgb0221
    Figure imgb0222
    90 2 n—Bu
    Figure imgb0223
    Figure imgb0224
    Figure imgb0225
    Figure imgb0226
    91 3 Me Direct bond H Ph Ph
    92 3 Me Direct bond H
    Figure imgb0227
    Figure imgb0228
    93 3 Me Direct bond H Ph
    Figure imgb0229
    94 3 Me Direct bond H Ph
    Figure imgb0230
    [Table 6]
    n R1, R2 X1 X2 Y1 Y2
    95 3 Me Direct bond H Ph
    Figure imgb0231
    96 3 Me Direct bond H Ph
    Figure imgb0232
    97 3 Me Direct bond H Ph
    Figure imgb0233
    98 3 Me Direct bond H Ph
    Figure imgb0234
    99 3 Me Direct bond H Ph
    Figure imgb0235
    100 3 Me Direct-bond H
    Figure imgb0236
    Figure imgb0237
    101 3 Me Direct bond Ph
    Figure imgb0238
    Figure imgb0239
    102 3 Me Direct bond Ph Ph
    Figure imgb0240
    103 3 Me Direct bond Ph Ph
    Figure imgb0241
    104 3 Me Direct bond Ph Ph
    Figure imgb0242
    105 3 Me Direct bond
    Figure imgb0243
    Figure imgb0244
    Figure imgb0245
    106 3 Me Direct bond
    Figure imgb0246
    Figure imgb0247
    Figure imgb0248
    107 3 Me Direct bond
    Figure imgb0249
    Figure imgb0250
    Figure imgb0251
    108 3 Me Direct bond
    Figure imgb0252
    Figure imgb0253
    Figure imgb0254
    109 3 Me
    Figure imgb0255
    H
    Figure imgb0256
    Figure imgb0257
    110 3 Me
    Figure imgb0258
    H Ph
    Figure imgb0259
    111 3 Me
    Figure imgb0260
    H Ph
    Figure imgb0261
    112 3 Me
    Figure imgb0262
    H Ph
    Figure imgb0263
    113 3 Me
    Figure imgb0264
    H Ph
    Figure imgb0265
    114 3 Me
    Figure imgb0266
    H Ph
    Figure imgb0267
    [Table 7]
    n R1, R2 X1 X2 Y1 Y2
    115 3 Me
    Figure imgb0268
    Ph
    Figure imgb0269
    Figure imgb0270
    116 3 Me
    Figure imgb0271
    Figure imgb0272
    Figure imgb0273
    Figure imgb0274
    117 3 Me
    Figure imgb0275
    Figure imgb0276
    Figure imgb0277
    Figure imgb0278
    118 3 Me
    Figure imgb0279
    Figure imgb0280
    Ph
    Figure imgb0281
    119 3 Me
    Figure imgb0282
    Figure imgb0283
    Figure imgb0284
    Figure imgb0285
    120 3 Me
    Figure imgb0286
    Figure imgb0287
    Ph
    Figure imgb0288
    121 3 Me
    Figure imgb0289
    H
    Figure imgb0290
    Figure imgb0291
    122 3 Me
    Figure imgb0292
    H
    Figure imgb0293
    Figure imgb0294
    123 3 Me
    Figure imgb0295
    Figure imgb0296
    Figure imgb0297
    Figure imgb0298
    124 3 Me
    Figure imgb0299
    H
    Figure imgb0300
    Figure imgb0301
    125 3 Me
    Figure imgb0302
    H
    Figure imgb0303
    Figure imgb0304
    126 3 Me
    Figure imgb0305
    H
    Figure imgb0306
    Figure imgb0307
    127 3 Me
    Figure imgb0308
    Figure imgb0309
    Figure imgb0310
    Figure imgb0311
    128 3 Me
    Figure imgb0312
    H
    Figure imgb0313
    Figure imgb0314
    129 3 Me
    Figure imgb0315
    H
    Figure imgb0316
    Figure imgb0317
    130 3 n-Bu
    Figure imgb0318
    H
    Figure imgb0319
    Figure imgb0320
    131 3 n-Bu
    Figure imgb0321
    Figure imgb0322
    Figure imgb0323
    Figure imgb0324
    [Table 8]
    n R1, R2 X1 X2 Y1 Y2
    132 3 Me Direct bond H Ph Ph
    133 3 Me Direct bond H
    Figure imgb0325
    Figure imgb0326
    134 3 Me Direct bond H Ph
    Figure imgb0327
    135 3 Me Direct bond H Ph
    Figure imgb0328
    136 3 Me Direct bond H Ph
    Figure imgb0329
    137 3 Me Direct bond H Ph
    Figure imgb0330
    138 3 Me Direct bond H Ph
    Figure imgb0331
    139 3 Me Direct bond H Ph
    Figure imgb0332
    140 3 Me Direct bond H Ph
    Figure imgb0333
    141 3 Me Direct bond H
    Figure imgb0334
    Figure imgb0335
    142 4 Me
    Figure imgb0336
    H
    Figure imgb0337
    Figure imgb0338
    143 4 Me
    Figure imgb0339
    H Ph
    Figure imgb0340
    144 4 Me
    Figure imgb0341
    H Ph
    Figure imgb0342
    145 4 Me
    Figure imgb0343
    Figure imgb0344
    Figure imgb0345
    Figure imgb0346
    146 4 Me
    Figure imgb0347
    Figure imgb0348
    Figure imgb0349
    Figure imgb0350
    147 4 Me
    Figure imgb0351
    Figure imgb0352
    Ph
    Figure imgb0353
    148 4 Me
    Figure imgb0354
    H
    Figure imgb0355
    Figure imgb0356
    149 4 Me
    Figure imgb0357
    H
    Figure imgb0358
    Figure imgb0359
    150 4 Me
    Figure imgb0360
    H
    Figure imgb0361
    Figure imgb0362
    [Table 9]
    n R1, R2 X1 X2 Y1 Y2
    151 4 Me
    Figure imgb0363
    H
    Figure imgb0364
    Figure imgb0365
    152 4 Me
    Figure imgb0366
    H
    Figure imgb0367
    Figure imgb0368
    153 4 Me
    Figure imgb0369
    H
    Figure imgb0370
    Figure imgb0371
    154 4 n—Bu
    Figure imgb0372
    H
    Figure imgb0373
    Figure imgb0374
    155 4 n—Bu
    Figure imgb0375
    Figure imgb0376
    Figure imgb0377
    Figure imgb0378
    Figure imgb0379
    Figure imgb0380
    Figure imgb0381
    Figure imgb0382
    [Table 10]
    p, q R3, R4 R5, R6 X3 X4 X5 Y3 Y4
    1 1, 1 Me Me Single bond
    Figure imgb0383
    H Me Ph
    2 1, 1 Me Me Single bond
    Figure imgb0384
    H Ph Ph
    3 1,1 Me Me Single bond
    Figure imgb0385
    H
    Figure imgb0386
    Figure imgb0387
    4 1, 1 Me n-Bu Single bond
    Figure imgb0388
    H
    Figure imgb0389
    Figure imgb0390
    5 1,1 n—Bu n-Bu Single bond
    Figure imgb0391
    H
    Figure imgb0392
    Figure imgb0393
    6 1, 1 Me Me Single bond
    Figure imgb0394
    H
    Figure imgb0395
    Figure imgb0396
    7 1, 1 Me Me Single bond
    Figure imgb0397
    H
    Figure imgb0398
    Figure imgb0399
    8 1, 1 Me Me Single bond
    Figure imgb0400
    H Ph
    Figure imgb0401
    9 1, 1 Me Me Single bond
    Figure imgb0402
    H Ph
    Figure imgb0403
    10 1,1 Me Me Single bond
    Figure imgb0404
    H Ph
    Figure imgb0405
    11 1, 1 Me Me Single bond
    Figure imgb0406
    H Ph
    Figure imgb0407
    12 1,1 Me Me Single bond
    Figure imgb0408
    H Ph
    Figure imgb0409
    13 1, 1 Me Me Single bond
    Figure imgb0410
    H Ph
    Figure imgb0411
    14 1,1 Me Me Single bond
    Figure imgb0412
    H Ph
    Figure imgb0413
    15 1,1 Me Me Single bond
    Figure imgb0414
    H
    Figure imgb0415
    Figure imgb0416
    16 1,1 Me Me Single bond
    Figure imgb0417
    H Ph
    Figure imgb0418
    17 1,1 Me Me Single bond
    Figure imgb0419
    H
    Figure imgb0420
    Figure imgb0421
    18 1,1 Me Me Single bond
    Figure imgb0422
    H Ph
    Figure imgb0423
    19 1,1 Me Me Single bond
    Figure imgb0424
    H
    Figure imgb0425
    Figure imgb0426
    20 1,1 Me Me Single bond
    Figure imgb0427
    H Ph
    Figure imgb0428
    21 1,1 Me Me Single bond
    Figure imgb0429
    H
    Figure imgb0430
    Figure imgb0431
    [Table 11]
    p, q R3, R4 R5, R6 X3 X4 X5 Y3 Y4
    22 1,1 Me Me Single bond
    Figure imgb0432
    H Ph
    Figure imgb0433
    23 1,1 Me Me Single bond
    Figure imgb0434
    H
    Figure imgb0435
    Figure imgb0436
    24 1,1 Me Me Single bond
    Figure imgb0437
    H Ph
    Figure imgb0438
    25 1, 1 Me Me Single bond
    Figure imgb0439
    H
    Figure imgb0440
    Figure imgb0441
    26 1, 1 Me Me Single bond
    Figure imgb0442
    H
    Figure imgb0443
    Figure imgb0444
    27 1,1 Me Me Single bond
    Figure imgb0445
    H Ph
    Figure imgb0446
    28 1,1 Me Me Single bond
    Figure imgb0447
    H
    Figure imgb0448
    Figure imgb0449
    29 1, 1 Me Me Single bond
    Figure imgb0450
    H Ph
    Figure imgb0451
    30 1,1 Me Me Single bond
    Figure imgb0452
    H
    Figure imgb0453
    Figure imgb0454
    31 1,1 Me Me Single bond
    Figure imgb0455
    H Ph
    Figure imgb0456
    32 1,1 Me Me Single bond
    Figure imgb0457
    H
    Figure imgb0458
    Figure imgb0459
    33 1,1 Me Me Single bond
    Figure imgb0460
    H
    Figure imgb0461
    Figure imgb0462
    34 1,2 Me Me Single bond
    Figure imgb0463
    H
    Figure imgb0464
    Figure imgb0465
    35 1,2 Me Me Single bond
    Figure imgb0466
    H Ph
    Figure imgb0467
    36 1,2 Me Me Single bond
    Figure imgb0468
    H Ph
    Figure imgb0469
    37 1,2 Me Me Single bond
    Figure imgb0470
    H Ph
    Figure imgb0471
    38 1,2 Me Me Single bond
    Figure imgb0472
    H
    Figure imgb0473
    Figure imgb0474
    39 1,2 Me Me Single bond
    Figure imgb0475
    H
    Figure imgb0476
    Figure imgb0477
    40 1,1 Me Me
    Figure imgb0478
    Figure imgb0479
    H
    Figure imgb0480
    Figure imgb0481
    41 1,1 Me Me
    Figure imgb0482
    Figure imgb0483
    H
    Figure imgb0484
    Figure imgb0485
    42 1,1 Me Me
    Figure imgb0486
    Figure imgb0487
    H
    Figure imgb0488
    Figure imgb0489
    [Table 12]
    p, q R3, R4 R5, R6 X3 X4 X5 Y3 Y4
    43 1,1 Me Me
    Figure imgb0490
    Figure imgb0491
    H
    Figure imgb0492
    Figure imgb0493
    44 1,1 Me n-Bu
    Figure imgb0494
    Figure imgb0495
    H
    Figure imgb0496
    Figure imgb0497
    45 1,1 n-Bu n-Bu
    Figure imgb0498
    Figure imgb0499
    H
    Figure imgb0500
    Figure imgb0501
    46 1,1 Me Me
    Figure imgb0502
    Figure imgb0503
    H
    Figure imgb0504
    Figure imgb0505
    47 1,1 Me Me
    Figure imgb0506
    Figure imgb0507
    H
    Figure imgb0508
    Figure imgb0509
    48 1,1 Me Me
    Figure imgb0510
    Figure imgb0511
    H
    Figure imgb0512
    Figure imgb0513
    49 1,1 Me Me
    Figure imgb0514
    Figure imgb0515
    H
    Figure imgb0516
    Figure imgb0517
    50 1,1 Me Me
    Figure imgb0518
    Figure imgb0519
    H
    Figure imgb0520
    Figure imgb0521
    51 1,1 Me Me
    Figure imgb0522
    Figure imgb0523
    H
    Figure imgb0524
    Figure imgb0525
    52 1,1 Me Me
    Figure imgb0526
    Figure imgb0527
    H
    Figure imgb0528
    Figure imgb0529
    53 1,1 Me Me
    Figure imgb0530
    Figure imgb0531
    H
    Figure imgb0532
    Figure imgb0533
    54 1,1 Me Me
    Figure imgb0534
    Figure imgb0535
    H
    Figure imgb0536
    Figure imgb0537
    55 1,1 Me Me
    Figure imgb0538
    Figure imgb0539
    H
    Figure imgb0540
    Figure imgb0541
    56 1, 1 Me Me
    Figure imgb0542
    Figure imgb0543
    H
    Figure imgb0544
    Figure imgb0545
    57 1,2 Me Me
    Figure imgb0546
    Figure imgb0547
    H
    Figure imgb0548
    Figure imgb0549
    58 1,2 Me Me
    Figure imgb0550
    Figure imgb0551
    H
    Figure imgb0552
    Figure imgb0553
    59 1,1 Me Me Single bond
    Figure imgb0554
    Ph
    Figure imgb0555
    Figure imgb0556
    60 1,1 Me Me Single bond
    Figure imgb0557
    Figure imgb0558
    Figure imgb0559
    Figure imgb0560
    61 1, 1 Me Me Single bond
    Figure imgb0561
    Figure imgb0562
    Figure imgb0563
    Figure imgb0564
    62 1,1 Me Me Single bond
    Figure imgb0565
    Figure imgb0566
    Figure imgb0567
    Figure imgb0568
    [Table 13]
    p, q R3, R4 R5, R6 X3 X4 X5 Y3 Y4
    63 1,1 Me Me Single bond
    Figure imgb0569
    Figure imgb0570
    Figure imgb0571
    Figure imgb0572
    64 1,1 Me Me Single bond
    Figure imgb0573
    Figure imgb0574
    Figure imgb0575
    Figure imgb0576
    65 1, 1 Me Me
    Figure imgb0577
    Figure imgb0578
    Figure imgb0579
    Figure imgb0580
    Figure imgb0581
    66 1,1 Me Me
    Figure imgb0582
    Figure imgb0583
    Figure imgb0584
    Figure imgb0585
    Figure imgb0586
    67 1,1 Me Me
    Figure imgb0587
    Figure imgb0588
    Figure imgb0589
    Figure imgb0590
    Figure imgb0591
    68 1,1 Me Me
    Figure imgb0592
    Figure imgb0593
    Figure imgb0594
    Figure imgb0595
    Figure imgb0596
    69 1,1 Me Me
    Figure imgb0597
    Figure imgb0598
    Figure imgb0599
    Figure imgb0600
    Figure imgb0601
    70 1,1 Me Me
    Figure imgb0602
    Figure imgb0603
    Figure imgb0604
    Figure imgb0605
    Figure imgb0606
    71 2,2 Me Me Single bond
    Figure imgb0607
    H Me Ph
    72 2,2 Me Me Single bond
    Figure imgb0608
    H Ph Ph
    73 2,2 Me Me Single bond
    Figure imgb0609
    H
    Figure imgb0610
    Figure imgb0611
    74 2,2 Me n-Bu Single bond
    Figure imgb0612
    H
    Figure imgb0613
    Figure imgb0614
    75 2,2 n-Bu n-Bu Single bond
    Figure imgb0615
    H
    Figure imgb0616
    Figure imgb0617
    76 2,2 Me Me Single bond
    Figure imgb0618
    H
    Figure imgb0619
    Figure imgb0620
    77 2,2 Me Me Single bond
    Figure imgb0621
    H
    Figure imgb0622
    Figure imgb0623
    78 2,2 Me Me Single bond
    Figure imgb0624
    H Ph
    Figure imgb0625
    79 2,2 Me Me Single bond
    Figure imgb0626
    H Ph
    Figure imgb0627
    80 2,2 Me Me Single bond
    Figure imgb0628
    H Ph
    Figure imgb0629
    81 2,2 Me Me Single bond
    Figure imgb0630
    H Ph
    Figure imgb0631
    82 2,2 Me Me Single bond
    Figure imgb0632
    H Ph
    Figure imgb0633
    83 2,2 Me Me Single bond
    Figure imgb0634
    H Ph
    Figure imgb0635
    84 2,2 Me Me Single bond
    Figure imgb0636
    H Ph
    Figure imgb0637
    Figure imgb0638
    Figure imgb0639
  • Next, the organic light-emitting device of the present invention will be described in detail.
  • The organic light-emitting device of the present invention is an organic light-emitting device comprising: a pair of electrodes which consist of an anode and a cathode, and one or more layers which are interposed between the electrodes and contain an organic compound, wherein at least one layer of the layers containing an organic compound contains at least one of the monoaminofluorene compounds represented by the above-mentioned general formula [1] or [2].
  • Moreover, it is preferable that the layer containing the compound represented by the above-mentioned general formula [1] or [2] contains at least one of the compounds represented by following general formulae [3] to [7], and it is more preferable that the layer containing the compound represented by the above-mentioned general formula [1] or [2] is a light-emitting layer.
    Figure imgb0640
    wherein Ar1 to Ar3 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and either one of them may be a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group; and R7 to R9 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
    Figure imgb0641
    wherein Ar4 to Ar7 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R10 and R11 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
    Figure imgb0642
    wherein Ar8 to Ar12 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R12 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
    Figure imgb0643
    wherein Ar13 to Ar16 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and up to any three of them may be a hydrogen atom, a halogen group, a substituted or unsubstituted alkyl group and a substituted or unsubstituted aralkyl group; and R13 to R16 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
    Figure imgb0644
    wherein R17 and R18 are groups selected from the group consisting of a hydrogen atom and substituted or unsubstituted alkyl, aralkyl and aryl groups, and R17's and R18's bound to different fluorene moieties may be the same or different and R17 and R18 bound to the same fluorene moiety may be the same or different; R19 to R22 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl and alkoxy groups, a substituted silyl group and a cyano group; and s is an integer of 2 to 5.
  • Although the compounds represented by general formulae [3] to [7] can be used for the purpose of both the dopant material and host material in a light-emitting layer respectively to obtain a device with high color purity, high luminescence efficiency and longer operating life, a device holding high color purity luminescence and having even higher luminescence efficiency can be obtained with the combination of a compound represented by the general formula [1] or [2] as a dopant material with a suitable host material which easily causes energy transfer, for example, the compounds represented by general formulae [3] to [7]. The dopant concentration in the host material is preferably from 0.01 % to 50 % by weight, more preferably from 0.5 % to 10 % by weight.
  • Specific examples of the substituents in general formulae [3] to [7] are the same as those referred to in the above-mentioned general formulae [1] and [2]. Typical examples of the compound represented by general formulae [3] to [7] are given below but the present invention is not limited to these.
    Figure imgb0645
    Figure imgb0646
    Figure imgb0647
    Figure imgb0648
    Figure imgb0649
    Figure imgb0650
    Figure imgb0651
    Figure imgb0652
    Figure imgb0653
    Figure imgb0654
    Figure imgb0655
    Figure imgb0656
    Figure imgb0657
    Figure imgb0658
    Figure imgb0659
    Figure imgb0660
    Figure imgb0661
    Figure imgb0662
    Figure imgb0663
    Figure imgb0664
    Figure imgb0665
    Figure imgb0666
    Figure imgb0667
    Figure imgb0668
    Figure imgb0669
    Figure imgb0670
    Figure imgb0671
    Figure imgb0672
    Figure imgb0673
    Figure imgb0674
    Figure imgb0675
    Figure imgb0676
    Figure imgb0677
    Figure imgb0678
    Figure imgb0679
    Figure imgb0680
    Figure imgb0681
    Figure imgb0682
    Figure imgb0683
    Figure imgb0684
    Figure imgb0685
    Figure imgb0686
    Figure imgb0687
    Figure imgb0688
    Figure imgb0689
    Figure imgb0690
    Figure imgb0691
  • The preferable examples of the organic light-emitting device of the present invention are shown in Figures 1 to 6.
  • Fig. 1 is a cross-sectional view showing an example of the organic light-emitting device according to the present invention. Figure 1 shows a structure in which an anode 2, a light-emitting layer 3 and a cathode 4 are formed on a substrate 1 in this order. The light-emitting device used here is useful in the case where it has all the properties of hole-transporting ability, electron-transporting ability and the light-emitting ability by itself, or in the case where compounds having each of these properties respectively are mixed and used.
  • Fig. 2 is a cross-sectional view showing another example of the organic light-emitting device according to the present invention. Figure 2 shows a structure in which an anode 2, a hole-transporting layer 5, an electron-transporting layer 6 and a cathode 4 are formed on a substrate 1 in this order. This structure is useful in the case where a light-emitting material having either one or both of hole-transporting ability and electron-transporting ability is used for the respective layer in combination with a hole-transporting or electron-transporting compound which has no light-emitting properties. A light-emitting layer 3 consists of either the hole-transporting layer 5 or the electron-transporting layer 6 in this case.
  • Fig. 3 is a cross-sectional view showing another example of the organic light-emitting device of the present invention. Figure 3 shows a structure in which an anode 2, a hole-transporting layer 5, a light-emitting layer 3, an electron-transporting layer 6 and a cathode 4 are formed on a substrate 1 in this order. Since this structure separates the functions of carrier transport and luminescence, it can be used in a suitable combination with compounds having hole-transporting ability, electron-transporting ability and light-emitting ability, thus extremely enhancing the flexibility of selection of materials and enabling various compounds which differ in luminescence wavelength to be used, thereby enabling diversification of luminescence hue. Furthermore, it also becomes possible to effectively confine each of the carriers or excitons in the light-emitting layer 3 positioned in the middle, and to aim at improvement in luminescence efficiency.
  • Fig. 4 is a cross-sectional view showing another example of the organic light-emitting device of the present invention. Figure 4 shows a structure in which a hole injecting layer 7 is inserted in the side of an anode 2 as compared with that of Figure 3 and that has an effect in improving the close contact of the anode 2 and a hole-transporting layer 5 or improving hole injecting properties and is effective for reduction in voltage.
  • Figs. 5 and 6 are cross-sectional views showing other examples of the organic light-emitting device of the present invention. Figs. 5 and 6 show structures in which a layer inhibiting holes or excitons from escaping to the side of a cathode 4 (hole blocking layer 8) is inserted between a light-emitting layer 3 and an electron-transporting layer 6, in comparison with the structures of Figures 3 and 4. By using a compound having a very high ionization potential as the hole blocking layer 8, these structures are effective for improving the luminescence efficiency.
  • However, Figs. 1 to 6 merely show very fundamental device structures, and the construction of the organic light-emitting device using the compound of the present invention is not limited to these. For example, various layer configurations can be taken including providing an insulating layer on the interface between the electrode and the organic layer, providing an adhesive layer or interference layer, or making a hole-transporting layer consisting of two layers different in ionization potential.
  • The monoaminofluorene compound represented by the general formula [1] or [2] used for the present invention can be used in any embodiment of Figs. 1 to 6.
  • Especially the organic layer using the compound of the present invention is useful as a light-emitting layer, an electron-transporting layer or a hole-transporting layer, and the layer formed by the vacuum evaporation method, the solution applying method or the like is excellent in stability with the passage of time since crystallization thereof cannot readily take place.
  • Although the present invention uses the monoaminofluorene compound represented by the general formula [1] or [2] particularly as a component of a light-emitting layer, it can also be used, if needed, together with a hole-transporting compound, a luminescent compound or an electron-transporting compound known in the art.
  • Examples of these compounds are given below.
  • Hole-transporting Compound
    Figure imgb0692
    Figure imgb0693
    Figure imgb0694
    Figure imgb0695
  • Electron-transporting Light-emitting Material
    Figure imgb0696
    Figure imgb0697
    Figure imgb0698
    Figure imgb0699
  • Light-emitting Material
    Figure imgb0700
    Figure imgb0701
    Figure imgb0702
    Figure imgb0703
  • Matrix Material of Light-emitting Layer and Electron-transporting Material
    Figure imgb0704
    Figure imgb0705
    Figure imgb0706
    Figure imgb0707
    Figure imgb0708
  • Hole-transporting Polymer Material
    Figure imgb0709
    Figure imgb0710
    Figure imgb0711
    Figure imgb0712
  • Light-emitting and Electron-transporting Polymer Material
    Figure imgb0713
    Figure imgb0714
  • In the organic light-emitting device of the present invention, the layer containing the monoaminofluorene compound represented by the general formula [1] or [2] and the layer consisting of other organic compounds can be generally formed into a thin film by the vacuum evaporation method or by the applying method by dissolving the compounds in a suitable solvent. When film forming is conducted especially by the applying method, the film can also be formed in combination with a suitable binding resin.
  • The above-mentioned binding resin can be selected from a wide range of binding resins and examples thereof include poly(vinyl carbazole) resin, polycarbonate resin, polyester resin, polyallylate resin, polystyrene resin, acrylic resin, methacrylic resin, butyral resin, poly(vinyl acetal) resin, diallyl phthalate resin, phenol resin, epoxy resin, silicone resin, polysulphone resin, urea resin, etc. but are not limited to these. These resins may be used alone or mixed as a copolymerized polymer of one or more types of them.
  • As an anode material, those having as high a work function as possible is suitable, and for example, a metal element such as gold, platinum, nickel, palladium, cobalt, selenium, and vanadium, or alloys thereof, and metal oxides such as tin oxide, zinc oxide, indium tin oxide (ITO) and indium zinc oxide can be used. Conductive polymers such as polyaniline, polypyrrole, polythiophene and polyphenylenesulfide can also be used. These electrode substances may be used alone and two or more of them can also be used in combination.
  • On the other hand, as a cathode material, those having a low work function is suitable and a metal element such as lithium, sodium, potassium, calcium, magnesium, aluminum, indium, silver, lead, tin and chromium or alloys of two or more thereof can be used. Use of a metal oxide such as indium tin oxide (ITO) is also possible. The cathode may be in a single layer structure or can take a multilayer structure.
  • Substrate used in the present invention is not limited, but a non-transparent plate such as metal substrate and ceramics substrate, a transparent plate such as glass, quartz, and a plastic sheet can be used. It is also possible to use a color filter film, a fluorescent color conversion filter film, a dielectric reflective film, etc. on the substrate to control the color of the emitted light.
  • In addition, a protection layer or seal layer can also be provided on the formed device in order to prevent contact with oxygen, moisture, etc. The protection layer may include inorganic material films such as a diamond thin film, a metal oxide film and a metal nitride film, polymer films such as those of a fluororesin, polyparaxylene, polyethylene, silicone resin and polystyrene resin as well as light curable resin, etc. Moreover, the device may be covered with glass, a gas impermeable film, metal, etc., and the device itself may be packaged in a suitable sealing resin.
  • Hereainfter, the present invention will be described by non-limiting examples still more specifically.
  • <Example 1> [Preparation process of example compound No. [1]-43]
  • Figure imgb0715
    Figure imgb0716
    2 g (6.25 mmol) of 2-iodo-9,9-dimethylfluorene and 1.5 g (4.12 mmol) of 2-(dihydroxyboranyl)-9,9-dimethylfluorene were dissolved in the mixed solvent (80 ml of degassed toluene and 40 ml of ethanol) and agitated under nitrogen flow, and 41 ml of sodium carbonate solution which was prepared by dissolving 9 g of anhydrous sodium carbonate in 45 ml of water was added dropwise thereto. After agitating for 30 minutes, 238 mg (0.206 mmol) of tetrakis(triphenylphosphine) palladium was added. Heating with agitation was carried out on the oil bath heated at 80°C for about 5 hours. After cooling the reaction solution to room temperature, 50 ml of water and 50 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, the aqueous layer was further extracted with toluene and ethyl acetate, and the extract combined with the above organic layer was dried over magnesium sulfate. The solvent was evaporated, the residual substance was refined by silica gel column chromatography (toluene:hexane = 1:2), and 1.5 g of bis(9,9-dimethylfluorene) was obtained.
  • 4.2 g (10.9 mmol) of bis (9,9-dimethylfluorene), 1.38 g (5.43 mmol) of iodine and 0.5 g of 50 % sulfuric acid were dissolved in 80 ml of methanol and agitated with heating on the oil bath heated at 60°C, and about 1 g of 35 % by weight aqueous hydrogen peroxide was added dropwise thereto. After cooling the reaction solution to room temperature, 30 ml of water was added and the deposited crude crystal was separated by filtration. The crude crystal was refined by silica gel column chromatography (toluene:hexane = 1:2), and 5.0 g of monoiodide of bis(9,9-dimethylfluorene) was obtained.
  • 113 mg (0.2 mmol) of palladium bis(benzylideneacetone) and 120 mg (0.6 mmol) of tri-tert-butylphosphine were dissolved in 40 ml of toluene under nitrogen flow, and agitated at room temperature for 15 minutes. 1.02 g (2 mmol) of monoiodide of bis(9,9-dimethylfluorene) dissolved in 50 ml of toluene was added dropwise thereto, and agitated for 30 minutes. 0.59 g (3 mmol) of bis(4-methylphenyl)amine dissolved in 50 ml of toluene was also added dropwise thereto, and subsequently 0.43 g (4.5 mmol) of sodium tert-butoxide was added. Heating with agitation was carried out on the oil bath heated at 120°C for about 8 hours. After cooling the reaction solution to room temperature, 50 ml of water was added, the aqueous layer and the organic layer were separated, the aqueous layer was further extracted with toluene and ethyl acetate, and the extract combined with the above organic layer was dried over magnesium sulfate. The solvent was evaporated, the residual substance was refined by silica gel column chromatography (toluene:hexane = 1:2), and 0.93 g of example compound [1]-43 was obtained.
  • <Example 2> [Preparation process of example compound No. [1]-60]
  • Figure imgb0717
  • 1.02 g (2 mmol) of monoiodide of bis(9,9-dimethylfluorene) and 0.97 g (3 mmol) of bis(4-methylphenyl)aminobenzene-4-boronic acid were dissolved and agitated under nitrogen flow in the mixed solvent (140 ml of degassed toluene and 70 ml of ethanol), and 30 ml of sodium carbonate solution which was prepared by dissolving 6 g of anhydrous sodium carbonate in 30 ml of water was added dropwise thereto. After agitating for 30 minutes, 174 mg (0.15 mmol) of tetrakis(triphenylphosphine) palladium was added. Heating with agitation was carried.out on the oil bath heated at 80°C for about 5 hours. After cooling the reaction solution to room temperature, 70 ml of water and 70 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, the aqueous layer was further extracted with toluene and ethyl acetate, and the extract combined with the above organic layer was dried over magnesium sulfate. The solvent was evaporated, the residual substance was refined by silica gel column chromatography (toluene:hexane = 1:2), and 1 g of example compound [1]-60 was obtained.
  • <Example 3> [Preparation process of example compound No. [2]-40]
  • Figure imgb0718
    6.94 g (21.7 mmol) of 2-iodo-9,9-dimethylfluorene and 1 g (7.25 mmol) of 1,4-phenylenebis(boronic acid) were dissolved and agitated under nitrogen flow in the mixed solvent (120 ml of degassed toluene and 60 ml of ethanol), and 145 ml of sodium carbonate solution which was prepared by dissolving 30 g of anhydrous sodium carbonate in 150 ml of water was added dropwise thereto. After agitating for 30 minutes, 840 mg (0.727 mmol) of tetrakis(triphenylphosphine) palladium was added. Heating with agitation was carried out on the oil bath heated at 80°C for about 3 hours. After cooling the reaction solution to room temperature, 50 ml of water and 50 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, the aqueous layer was further extracted with toluene and ethyl acetate, and the extract combined with the above organic layer was dried over magnesium sulfate. The solvent was evaporated, the residual substance was refined by silica gel column chromatography (toluene:hexane = 1:2), and 3.02 g of 1,4-phenylenebis(9,9-dimethylfluorene) was obtained.
  • 5.04 g (10.9 mmol) of 1,4-phenylenebis(9,9-dimethylfluorene), 1.38 g (5.43 mmol) of iodine and 0.5 g of 50% sulfuric acid were dissolved in 120 ml of methanol. Heating with agitation was carried out on the oil bath heated at 60°C, and about 1 g of 35 wt% aqueous hydrogen peroxide was added dropwise thereto. After cooling the reaction solution to room temperature, 30 ml of water was added and the deposited crude crystal was separated by filtration. The crude crystal was refined by silica gel column chromatography (toluene:hexane = 1:2), and 5.9 g of monoiodide of 1,4-phenylenebis(9,9-dimethylfluorene) was obtained.
  • 1.18 g (2 mmol) of monoiodide of 1,4-phenylenebis (9,9-dimethylfluorene) and 0.97 g (3 mmol) of bis (4-methylphenyl) aminobenzene-4-boronic acid were dissolved and agitated under nitrogen flow in the mixed solvent (100 ml of degassed toluene and 50 ml of ethanol), and 30 ml of sodium carbonate solution which was prepared by dissolving 6 g of anhydrous sodium carbonate in 30 ml of water was added dropwise thereto. After agitating for 30 minutes, 174 mg (0.15 mmol) of tetrakis(triphenylphosphine) palladium was added. Heating with agitation was carried out on the oil bath heated at 80°C for about 5 hours. After cooling the reaction solution to room temperature, 60 ml of water and 60 ml of ethyl acetate were added, the aqueous layer and the organic layer were separated, the aqueous layer was further extracted with toluene and ethyl acetate, and the extract combined with the above organic layer was dried over magnesium sulfate. The solvent was evaporated, the residual substance was refined by silica gel column chromatography (toluene:hexane = 1:2), and 1.09 g of example compound [2]-40 was obtained.
  • <Example 4>
  • The organic light-emitting device of the structure shown in Figure 3 was prepared by the process shown below.
  • A glass substrate as the substrate 1 on which a film of indium tin oxide (ITO) having a film thickness of 120 nm as the anode 2 was formed by sputtering method was used as a transparent conductive support substrate. This substrate was subjected to ultrasonic washing in acetone and isopropyl alcohol (IPA) subsequently, boil-washed in IPA and dried. It was further subjected to UV/ozone washing and used as a transparent conductive support substrate.
  • The compound shown by the following structural formula was used as a hole-transporting material and a chloroform solution thereof was adjusted so that the concentration thereof was 0.5 % by weight.
    Figure imgb0719
  • This solution was dropped on the above ITO electrode (anode 2), and spin coating was performed first by rotation at 500 RPM for 10 seconds followed by rotation at 1000 RPM for 1 minute to form a film. It was subsequently dried in a vacuum oven at 80°C for 10 minutes, and the solvent in the thin film was removed completely. The thickness of the formed TPD film (hole-transporting layer 5) was 50 nm.
  • Next, vacuum evaporation of the above-mentioned example compound No. [1]-43 was carried out to deposit the compound on the hole-transporting layer 5, and the 20 nm-thick light-emitting layer 3 was formed. The degree of vacuum at the time of vacuum evaporation was 1.0×10-4 Pa, and the film forming speed was 0.2 to 0.3 nm/sec.
  • Furthermore, aluminum quinolinol (Alq3) was formed into a film of 40 nm in thickness as an electron-transporting layer 6 by vacuum evaporation method. The degree of vacuum at the time of the vacuum evaporation of these organic layers was 1.0×10-4 Pa, and the film forming speed was 0.2 to 0.3 nm/sec.
  • Next, using the vacuum evaporation source material consisting of an aluminum-lithium alloy (lithium concentration 1 atom%), a metal film with a thickness of 10 nm was formed by vacuum evaporation method on the above organic layer, the aluminum film with a thickness of 150 nm was further prepared by vacuum evaporation method, and the organic light-emitting device comprising an aluminum-lithium alloy film as an electron injection electrode (cathode 4) was prepared. The degree of vacuum at the time of vacuum evaporation was 1.0×10-4 Pa, and the film forming speed was 1.0 to 1.2 nm/sec.
  • The obtained organic EL device was covered with a glass plate for protection in dry air atmosphere, and sealed with an acrylic resin based adhesive so that the device might not be degraded by adsorption of moisture.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, and blue luminescence of 780 cd/m2 of luminance, maximum luminance of 5900 cd/m2, and luminescence efficiency 0.73 lm/W were observed.
  • (Examples 5 to 13)
  • Devices were formed in the same way as in Example 4 except that example compound [1]-43 was replaced with the example compounds shown in Table 14 and evaluated in the same way. The results are shown in Table 14. [Table 14]
    Example Example compound No. Applied voltage (V) Luminance (cd/m2) Maximum luminance (cd/m2) Efficiency (lm/W)
    5 [1]-16 7 680 5000 0. 57
    6 [1]-49 6 880 6700 0. 75
    7 [1]-60 6 840 6100 0. 83
    8 [1]-92 6 900 6600 0. 77
    9 [1]-95 6 1000 6800 0. 85
    10 [1]-58 6 820 6400 0. 72
    11 [2]-17 6 820 5700 0. 80
    12 [2]-65 6 980 6800 0. 87
    13 [2]-85 6 810 5900 0. 68
  • (Example 14)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-60 and example compound No. [3]-1 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 4200 cd/m2 of luminance, maximum luminance of 9600 cd/m2, and luminescence efficiency 1.20 lm/W were observed.
  • (Examples 15 to 23)
  • Devices were formed in the same way as in Example 10 except that example compound [1]-60 was replaced with the example compounds shown in Table 15 and evaluated in the same way. The results are shown in Table 15. [Table 15]
    Example Example compound No. Applied voltage (V) Luminance (cd/m2) Maximum luminance, (cd/m2) Efficiency (lm/W)
    15 [1]-6 7 2900 6500 0. 67
    16 [1]-47 6 6800 17200 1. 74
    17 [1]-49 6 6300 16600 1. 62
    18 [1]-80 6 5100 11500 1. 30
    19 [1]-91 6 5200 13100 1. 42
    20 [1]-99 6 6900 16500 1. 80
    21 [2]-17 6 4600 11700 1. 28
    22 [2]-65 6 6100 14200 1. 52
    23 [2]-85 6 5100 11900 1. 39
  • (Example 24)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-43 and example compound No. [3]-15 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 3900 cd/m2 of luminance, maximum luminance of 10500 cd/m2, and luminescence efficiency 1.12 lm/W were observed.
  • (Example 25)
  • A device was formed in the same way as in Example 24 except that example compound No. [1]-43 was replaced with example compound No. [2]-40.
  • The thus obtained device along with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode was used on the applied voltage of 6 V, and blue luminescence of 4200 cd/m2 of luminance, maximum luminance of 13100 cd/m2, and luminescence efficiency 1.125 lm/W were observed.
  • (Example 26)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-92 and example compound No. [4]-1 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 6000 cd/m2 of luminance, maximum luminance of 12200 cd/m2, and luminescence efficiency 1.45 lm/W were observed.
  • (Examples 27 to 30)
  • Devices were formed in the same way as in Example 26 except that example compound No. [1]-92 was replaced with the example compounds shown in Table 16 and evaluated in the same way. The results are shown in Table 16. [Table 16]
    Example Example compound No. Applied voltage (V) Luminance (cd/m2) Maximum luminance (cd/m2) Efficiency (lm/W)
    27 [1]-66 6 5600 11800 1. 33
    28 [1]-158 6 3900 9800 1. 17
    29 [2]-17 6 5300 14100 1. 47
    30 [2]-65 6 6600 15400 1. 61
  • (Example 31)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-60 and the above-mentioned example compound No. [5]-1 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 4500 cd/m2 of luminance, maximum luminance of 13700 cd/m2, and luminescence efficiency 1.35 lm/W were observed.
  • (Example 32)
  • A device was formed in the same way as in Example 31 except that example compound No. [1]-60 was replaced with example compound No. [2]-40.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 4900 cd/m2 of luminance, maximum luminance of 15200 cd/m2, and luminescence efficiency 1.45 lm/W were observed.
  • (Example 33)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-60 and example compound No. [6]-2 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device along with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 4700 cd/m2 of luminance, maximum luminance of 15800 cd/m2, and luminescence efficiency 1.65 lm/W were observed.
  • (Example 34)
  • A device was formed in the same way as in Example 33 except that example compound No. [6]-2 was replaced with example compound No. [6]-9.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 5900 cd/m2 of luminance, maximum luminance of 18200 cd/m2, and luminescence efficiency 1.85 lm/W were observed.
  • (Example 35)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-92 and the above-mentioned example compound No. [7]-1 were co-deposited (5:100 in weight ratio) to form 20 nm light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 5100 cd/m2 of luminance, maximum luminance of 12300 cd/m2, and luminescence efficiency 1.38 lm/W were observed.
  • (Examples 36 to 43)
  • The luminescence spectra of the devices formed in Examples 4, 15, 21, 26, 31, 33, 34 and 35 were observed by MCPD-7000 and the CIE chromaticity coordinates were measured. The results are shown in Table 17. [Table 17]
    Example Device example No. CIE chromaticity coordinate (x, y)
    36 4 0.15,0.10
    37 15 0.15,0.10
    38 21 0.15,0.11
    39 26 0.15,0,10
    40 31 0.16,0.10
    41 33 0.15,0.09
    42 34 0.15,0.09
    43 35 0.15,0.11
  • (Example 44)
  • A device was formed in the same way as in Example 4 except that example compound No. [7]-1 and example compound No. [2]-65 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 4700 cd/m2 of luminance, maximum luminance of 11100 cd/m2, and luminescence efficiency 1.30 lm/W were observed.
  • (Example 45)
  • A device was formed in the same way as in Example 4 except that example compound No. [1]-43 and example compound No. [2]-65 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 6V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, blue luminescence of 5900 cd/m2 of luminance, maximum luminance of 12600 cd/m2, and luminescence efficiency 1.39 lm/W were observed.
  • (Example 46)
  • Voltage was applied to the device formed in Example 13 for 100 hours under nitrogen atmosphere while maintaining the current density at 7.0 mA/cm2 and degradation in luminance was found to be small as the initial luminance of 480 cd/m2 was changed to 420 cd/m2 after 100 hours.
  • (Comparative Example 1)
  • A device was formed in the same way as in Example 4 except that the following styryl compound was used as a light-emitting layer.
    Figure imgb0720
  • 10V was applied to the thus obtained device by using an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, greenish blue white luminescence of 120 cd/m2 of luminance, maximum luminance of 3800 cd/m2, and luminescence efficiency 0.17 lm/W were observed.
  • (Comparative Example 2)
  • A device was formed in the same way as in Example 4 except that the above styryl compound and example compound No. [4]-1 were co-deposited (5:100 in weight ratio) to form 20 nm-thick light-emitting layer 3.
  • 10V was applied to the thus obtained device along with an ITO electrode (anode 2) as a positive electrode and an Al-Li electrode (cathode 4) as a negative electrode. As the result, greenish blue white luminescence of 125 cd/m2 of luminance, maximum luminance of 4500 cd/m2, and luminescence efficiency 0.30 lm/W were observed.
  • (Comparative Example 3)
  • The luminescence spectrum of the device formed in Comparative Example 2 was observed by MCPD-7000 and the CIE chromaticity coordinate measured was (x,y) = (0.16, 0.30).
  • As described by way of embodiments and examples, the organic light-emitting device using the monoaminofluorene compound represented by the general formula [1] or [2] of the present invention, used in a single layer or in a mixed layer of dopant/host, enables high luminance luminescence when applied with a low voltage and is also excellent in color purity and durability. Furthermore, the device can be formed using vacuum evaporation, the casting method or the like, and a device having a large area can be readily produced at a relatively low cost.
  • This application is a divisional application of the European patent application no. 03791210.2 (the "parent application"), also published under no. EP-A-1542962 . The content of the original claims of the parent application is repeated below in the present description and form part of the content of this description as follows:
  • ITEMS
  1. 1. A monoaminofluorene compound represented by the following general formula [1]:
    Figure imgb0721
    wherein X1 is a divalent group selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, and alkylene, aralkylene, alkenylene, amino, silyl, carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, or X1 and may be a direct bond;
    X2 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group and a cyano group;
    Y1 and Y2 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y1 and Y2, or X1, Y1 and Y2 may also join together to form a ring;
    R1 and R2 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    n is an integer of 2 to 10 when X1 is a direct bond and X2 is a hydrogen atom, and otherwise an integer of 1 to 10.
  2. 2. A monoaminofluorene compound represented by the following general formula [2]:
    Figure imgb0722
    wherein X3 and X4 may be the same or different and are divalent groups selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, unsubstituted carbonyl, ether and thioether groups, or X3 may be a direct bond;
    X5 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group, and a cyano group;
    Y3 and Y4 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y3 and Y4, or X3, Y3 and Y4 may also join together to form a ring;
    R3 to R6 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    each of p and q is an integer not less than one and p+q is an integer of 2 to 10.
  3. 3. An organic light-emitting device comprising: a pair of electrodes which consist of an anode and a cathode, and one or more layers which are interposed between the electrodes and contain an organic compound, wherein at least one of the layers containing the organic compound contains at least one compound represented by the general formula [1]:
    Figure imgb0723
    where X1 is a divalent group selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, and alkylene, aralkylene, alkenylene, amino, silyl, carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring groups, or X1 may be a direct bond;
    X2 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group and a cyano group;
    Y1 and Y2 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y1 and Y2, or X1, Y1 and Y2 may also join together to form a ring;
    R1 and R2 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    n is an integer of 2 to 10 when X1 is a direct bond and X2 is a hydrogen atom, and otherwise an integer of 1 to 10.
  4. 4. An organic light-emitting device comprising: a pair of electrodes which consist of an anode and a cathode, and one or more layers which are interposed between the electrodes and contain an organic compound, wherein at least one of the layers containing the organic compound contains at least one compound represented by the general formula [2]:
    Figure imgb0724
    where X3 and X4 may be the same or different and are divalent groups selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, unsubstituted carbonyl, ether and thioether groups, or X3 may be a direct bond;
    X5 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group, and a cyano group;
    Y3 and Y4 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y3 and Y4, or X3, Y3 and Y4 may also join together to form a ring;
    R3 to R6 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    each of p and q is an integer not less than one and p+q is an integer of 2 to 10.
  5. 5. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] contains at least one compound represented by the following general formula [3]:
    Figure imgb0725
    where Ar1 to Ar3 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and either one of them may be a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group; and R7 to R9 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or .unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
  6. 6. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] contains at least one compound represented by the following general formula [3]:
    Figure imgb0726
    where Ar1 to Ar3 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and either one of them may be a hydrogen atom, a substituted or unsubstituted alkyl group, or a substituted or unsubstituted aralkyl group; and R7 to R9 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
  7. 7. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] contains at least one compound represented by the following general formula [4]:
    Figure imgb0727
    where Ar4 to Ar7 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R10 and R11 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
  8. 8. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] contains at least one compound represented by the following general formula [4]:
    Figure imgb0728
    where Ar4 to Ar7 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R10 and R11 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl groups, a substituted amino group and a cyano group.
  9. 9. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] contains at least one compound represented by the following general formula [5]:
    Figure imgb0729
    where Ar8 to Ar12 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R12 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
  10. 10. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] contains at least one compound represented by the following general formula [5]:
    Figure imgb0730
    where Ar8 to Ar12 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups; and R12 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
  11. 11. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] contains at least one compound represented by the following general formula [6]:
    Figure imgb0731
    where Ar13 to Ar16 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and up to any three of them may be a hydrogen atom, a halogen group, a substituted or unsubstituted alkyl group and a substituted or unsubstituted aralkyl group; and R13 to R16 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
  12. 12. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] contains at least one compound represented by the following general formula [6]:
    Figure imgb0732
    where Ar13 to Ar16 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted aryl and heterocyclic ring groups, and up to any three of them may be a hydrogen atom, a halogen group, a substituted or unsubstituted alkyl group and a substituted or unsubstituted aralkyl group; and R13 to R16 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, a substituted amino group and a cyano group.
  13. 13. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] contains at least one compound represented by the following general formula [7]:
    Figure imgb0733
    where R17 and R18 are groups selected from the group consisting of a hydrogen atom and substituted or unsubstituted alkyl, aralkyl and aryl groups, and R17's and R18's bound to different fluorene moieties may be the same or different and R17 and R18 bound to the same fluorene moiety may be the same or different; and R19 to R22 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl and alkoxy groups, a substituted silyl group and a cyano group; and s is an integer of 2 to 5.
  14. 14. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] contains at least one compound represented by the following general formula [7]:
    Figure imgb0734
    where R17 and R18 are groups selected from the group consisting of a hydrogen atom and substituted or unsubstituted alkyl, aralkyl and aryl groups, and R17's and R18's bound to different fluorene moieties may be the same or different and R17 and R18 bound to the same fluorene moiety may be the same or different; R19 to R22 are groups selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl and aralkyl and alkoxy groups, a substituted silyl group and a cyano group; and s is as integer of 2 to 5.
  15. 15. The organic light-emitting device according to item 3, wherein the layer containing the compound represented by the general formula [1] is a light-emitting layer.
  16. 16. The organic light-emitting device according to item 4, wherein the layer containing the compound represented by the general formula [2] is a light-emitting layer.

Claims (2)

  1. A monoaminofluorene compound represented by the general formula [1]:
    Figure imgb0735
    in which n, R1, R2, X1, X2, Y1 and Y2 have the following meaning: n R1, R2 X1 X2 Y1 Y2 43 2 Me Direct bond H
    Figure imgb0736
    Figure imgb0737
    47 2 Me Direct bond H Ph
    Figure imgb0738
    49 2 Me Direct bond H Ph
    Figure imgb0739
    60 2 Me
    Figure imgb0740
    H
    Figure imgb0741
    Figure imgb0742
    91 3 Me Direct bond H Ph Ph 92 3 Me Direct bond H
    Figure imgb0743
    Figure imgb0744
    95 3 Me Direct bond H Ph
    Figure imgb0745
    99 3 Me Direct bond H Ph
    Figure imgb0746
  2. An organic light-emitting device comprising: a pair of electrodes which consist of an anode and a cathode, and one or more layers which are interposed between the electrodes and contain an organic compound, wherein at least one of the layers containing the organic compound contains at least one compound represented by the general formula [1]:
    Figure imgb0747
    where X1 is a divalent group selected from the group consisting of substituted or unsubstituted alkylene, aralkylene, arylene and heterocyclic ring groups, and alkylene, aralkylene, alkenylene, amino, silyl, carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring groups, or X1 may be a direct bond;
    X2 is a group selected from the group consisting of a hydrogen atom, a halogen group, substituted or unsubstituted alkyl, aralkyl, alkenyl, alkynyl, alkoxy, aryl, heterocyclic ring and sulfide groups, a substituted silyl group and a cyano group;
    Y1 and Y2 may be the same or different and are groups selected from the group consisting of substituted or unsubstituted alkyl, aralkyl, aryl and heterocyclic ring groups, substituted or unsubstituted alkylene, aralkylene, alkenylene, amino and silyl groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group, and unsubstituted carbonyl, ether and thioether groups having a linking group consisting of a substituted or unsubstituted arylene or divalent heterocyclic ring group;
    Y1 and Y2, or X1, Y1 and Y2 may also join together to form a ring;
    R1 and R2 may be the same or different and are groups selected from the group consisting of a hydrogen atom, and substituted or unsubstituted alkyl, aralkyl and aryl groups; and
    n is an integer of 2 to 10 when X1 is a direct bond and X2 is a hydrogen atom, and otherwise an integer of 1 to 10,
    wherein the layer containing the compound represented by the general formula [1] further contains at least one compound represented by the following formulae [3]-1, [3]-15, [4]-1, [5]-1, [6]-2, [6]-9 and [7]-1:
    Figure imgb0748
    Figure imgb0749
    Figure imgb0750
    Figure imgb0751
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